How do I even start the conversation as a tenant?

Here are some financing options to consider:HELOC or Cash-Out Refi on Another Property – If you or your mom have equity elsewhere, this could be a more flexible and lower-interest option.Business Line of Credit – Since the property is in an LLC, you might qualify for a business LOC, which could cover construction costs.Private Money Lender – If you’re okay with 12-15% rates, a private lender could fund this as a short-term loan, especially if the guesthouse will generate strong income.Construction Loan – Some lenders offer short-term construction financing, which converts to a longer-term mortgage once completed.Seller/Partner Financing – Bringing in an investor or structuring a joint venture with someone willing to fund the build in exchange for a share of the income.Credit Card Stacking or Unsecured Business Loans – Riskier but could work if you need to bridge a gap until the unit starts cash flowing.Would love to hear more details—especially your timeline and expected rental income.

Since I’m holding these properties for the long term (30-year loans), I’ll have fully paid-off assets around the same time I’d traditionally start withdrawing from my 401(k).

Hey AudreyHere's a list of things you should look for in your investment properties...Start by assessing the property’s curb appeal and exterior condition, checking the roof for damage and foundation for cracks or moisture.

You can start to educate yourself on the individual components; how much does it cost to paint on a per sqft basis or what is an average kitchen remodel.  

It’s a beautiful old house and would be a real gem if it was restored, but I don’t have the funds or a credit score good enough to get a loan that big (without an insane amount of interest tacked on).I’m hoping to turn someone on to it who loves restoring old properties, or start investing in a group that does and tell them about my house and invest as a team.

When I first started out, I was insuring everything with USAA.

@Chloe Salcedoi'd start with a house hack.

So, if you start with a duplex, your next purchase could be a triplex or fourplex.

8 in 24 months is no joke, especially chipping away one at a time, I'm sure it has come with plenty of teachable moments, but its awesome that you are able to ask the question of how to scale.To start, a hard money lender that is only allowing you to do one at a time with your track record is... well... kind of silly.